4-Fluorobenzyl chloride → 1-(4-fluorobenzyl)-2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine

HRID 1437473Notes

Reaction equation

HRID 1437473 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:10][C:11]3[C:12]([N:23]=2)=[N:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=3)[CH:6]=[CH:7][CH:8]=1.[B].C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.[F:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48]Cl)=[CH:46][CH:45]=1>CN(C)C=O>[F:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48][N:10]2[C:11]3[C:12](=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:16]=3)[N:23]=[C:9]2[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 96024-Fluorobenzyl chlorideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine2×HCID 5462311BoronHCID 99483042-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine

Product 1

HCID 230261211-(4-fluorobenzyl)-2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Example 1) (80 mg), 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine resin (PS-BEMP, 2.2 mmol/g) (181 mg) and N,N-dimethyl formamide (3.2 ml) was shaken at room temperature for 1 hour. To the mixture was added 4-fluorobenzyl chloride (46 mg), and the mixture was further shaken at room temperature for 15 hours. The resin was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to a preparative HPLC, and the desired fraction was concentrated. The concentrate was distributed into dichloromethane and a saturated aqueous solution of sodium bicarbonate. The organic layer was filtered by means of a PTFE filter tube, and concentrated under reduced pressure to obtain 1-(4-fluorobenzyl)-2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine (84 mg, 78%).

Workup

  1. stirringthe mixture was further shaken at room temperature for 15 hours
  2. filtrationThe resin was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. concentrationthe desired fraction was concentrated
  5. filtrationThe organic layer was filtered by means of a PTFE
  6. filtrationfilter tube
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04c9820d5abc4b848a99a0060a03f8d4
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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